(tl:dr get functional clothes that pack small and perform multiple purposes, be organized, don't weigh yourself down with things that perform only one function.)
1) Pack small. Don't check bags.
Checking bags is a hassle -- it slows you down getting on and off of the plane and the airline can misplace your luggage, lots of airlines charge for checked bags now and someone has to carry all that stuff once you get wherever you're going. When I travel I want to be able to carry everything that I'm going to use with me, like a snail. Or a turtle. Or a flying turtle, like Gamera. This limits you to one carry on and one "small personal item". So you need to be able to fit all your gear and your clothes into a small space. This is particularly difficult for photographers who are carrying dozens of pounds of gear as well as the stuff everybody else brings with them ordinarily.
Here's me in an airport with all my camera gear in a Loweprow AW Trekker, sometime in 2011.
It's made for cameras and also has a laptop bag slot, which you can also stuff with clothes.
Backpacks are efficient and good for carrying your gear when you get to your destination,
but they're more fatiguing than a rollerbag.
Clickenzee to Embiggen!
2) Buy clothes made for backpackers.
Why re-invent the wheel? Backpackers have been trying to get things small since the backpack was invented. Cotten is right out, it's bulky and it takes a long time to dry. Polyester clothes you can wash in the sink at night, hang them on a towel rack and they'll be dry in the morning. I usually bring two pairs of cargo pants, three shirts, and two pairs of travel underwear. You wash one set of everything each night and rotate between three shirts so it doesn't look like you have the worlds most limited wardrobe. Here's a link to some EMS camp cargo pants, if you're reading this in the future and the EMS link is dead, they're cargo pants made out of really thin fabric that roll up about 50% smaller than a pair of denim jeans and weigh maybe 1/3 of what jeans do. You want these.
3) Use packing cubes.
Packing cubes not only keep things organized, but they keep stuff compressed.
You can find them at places like Eastern Mountain Sports or REI. Bring an empty cube to keep your dirty clothes in.
Small Eagle Creek packing cube with a pair of pants and a shirt stuffed in.
You can make it smallllll. Clickenzee to Embiggen!
4) They don't count your clothes as a carry on.
This is the Big Secret so I'm bolding it. If you're wearing it, they don't count it. So buy yourself a Domke PhoTogs vest.
I have a messenger style camera bag and this is what I usually carry around with me. One camera, (two if you count the iPhone, and I've used it before), five lenses some batteries, storage, a first aid kit (the green thing) with pain killers, antacids, anti diarrhea meds, decongestants, emergency money (bills and change), Band Aids, allergy pills and some sleeping pills.)
This is usually my "personal item". Clickenzee to Embiggen!
Having a camera bag like this kind of screws your "personal item" that other people might use to carry around important shiznit. So, I take everything out of my camera bag and put it in the vest. Now you've got all your gear with you if you need it and you can either stuff your empty messenger bag in your other carry on and bring a larger duffle bag, or put more stuff in your carryon.
Likewise, don't put that bulky sweater in your suitcase, wear it on to the plane. If it's too warm, tie it around your waist.
Everything in the vest, now you get a whole new "personal item". Clickenzee to Embiggen!
5) You don't have to put your bag in the overhead over your own seat.
There are fewer overhead bins at the back of the plane, in fact, the last two rows don't usually have any. That's where they store some of the emergency equipment and the crew's bags are often there too. When getting on the plane scope out the overhead space on the way to your seat, if the bin is already full where you're sitting, put your bag in the next space you pass. You don't want your bag full of zillion dollar lenses to get gate checked and returned to you like a bag of broken light bulbs. (In addition, the first few rows on some planes have slightly smaller overheads due to the curvature of the fuselage.)
6) Get an e-reader.
Yes, I know how cool you look reading a tattered trade paperback o Tristram Shandy but books will weigh you down faster than anything else. If you need to put a sticker on the back of your iPad that says "NOT READING 50 SHADES OF GREY" but suck it up and leave the books at home. Before you got to 10,000 feet you can look at the in-flight catalog and wonder who on Earth buys that crap.
7) Pack things you can't get at your destination.
It's really easy to borrow a shirt from someone when you get to Tulsa, or to buy one at ye local store, it's more difficult to get a charger for your sony Mavica, so pack that first.
8) Pack food.
Pack portable food that will keep, like energy bars. Fruit is nice but it's destroyed too easily banging around in your luggage. Don't pack something that's going to make you thirsty, like a jar of salted peanuts.
9) Leave your core travel items in your luggage.
You know that stuff you need every time you travel? Your toothbrush, your swim suit (there will be a hot tub at the hotel if you don't pack it, plus it doubles as "lounging around" wear while you're washing your pants) your first aid kit, your business cards, and model releases -- keep all that stuff in your bag all the time. (Roswell here is sitting on the nail clippers.) This save a bunch of time while you're packing. I also leave a travel cube with underwear and socks in my bag so when it's time to go you don't need to wonder if you've packed that stuff.
Leave your core items packed. Clickenzee to Embiggen!
10) Always have enough gear on your person to get the assignment done if you lose all the rest of your stuff.
My grandfather was an electrician who always used to say "study the hazards" -- which is useful advice. When you're packing you should be thinking "what happens if..." -- What happens if you lose that suitcase? What happens if that camera stops working? What happens if your card reader dies?
I bring a backup of everything critical -- which means an extra camera, extra memory, extra batteries, so that if something stops working you don't need to worry about trying to fix it while people are tapping their toes and staring at you, you just swap it out.
On the left here is the gear that I packed for a roller derby portrait shoot in Minnesota, it's everything that I needed to get the job done awesomely. On the right is a backup kit that I could do the job with if somehow the airline lost all my gear. Bringing a backup doesn't mean a duplicate. If your main camera is a big gigantic DSLR, you don't need another one of the same model, you can pack a smaller camera. Enough to get the job done.
Bring Backups. Clickenzee to Embiggen!
So that's it. Get small stuff, pack it tight, keep it with you, don't bring things you don't need. The goal is coming back with the pictures. It's very easy to pack way more clothes than you need.
Patrick Rhone adds this link to a post where he's collected rewviews of "traveling pants".
Someone had asked about traveling with numerous bottles of medicine and the large amount of space taken up by mostly empty bottles. Thanks to Jennifer E. Carr from Facebook who says: "I am a Pharmacy Tech (in my other life) and we will put medications into plastic bags with all the information you need to get through the airport." And this from Celeste Young "you can also get blister packs done up on the weekly with an 'official' print out of all the meds taken."
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